Literature DB >> 20346874

Synthesis and evaluation of new imaging agent for central nicotinic acetylcholine receptor α7 subtype.

Mikako Ogawa1, Shingo Nishiyama, Hideo Tsukada, Kentaro Hatano, Takeshi Fuchigami, Hiroshi Yamaguchi, Yoshitaka Matsushima, Kengo Ito, Yasuhiro Magata.   

Abstract

INTRODUCTION: The nicotinic acetylcholine receptor (nAChR) alpha7 subtype (alpha(7) nAChR) is one of the major nAChR subtypes in the brain. We synthesized C-11 labeled alpha(7) nAChR ligands, (R)-2-[(11)C]methylamino-benzoic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester ([(11)C](R)-MeQAA) and its isomer (S)-[(11)C]MeQAA, for in vivo investigation with positron emission tomography (PET). Then, the potential of (R)- and (S)-[(11)C]MeQAA for in vivo imaging of alpha(7) nAChR in the brain was evaluated in mice and monkeys.
METHODS: The binding affinity for alpha(7) nAChR was measured using rat brain. Biodistribution and in vivo receptor blocking studies were undertaken in mice. Dynamic PET scans were performed in conscious monkeys.
RESULTS: The affinity for alpha(7) nAChR was 41 and 182 nM for (R)- and (S)-MeQAA, respectively. The initial uptake in the mouse brain was high ([(11)C](R)-MeQAA: 7.68 and [(11)C](S)-MeQAA: 6.65 %dose/g at 5 min). The clearance of [(11)C](R)-MeQAA was slow in the hippocampus (alpha(7) nAChR-rich region) but was rapid in the cerebellum (alpha(7) nAChR-poor region). On the other hand, the clearance was fast for [(11)C](S)-MeQAA in all regions. The brain uptake of [(11)C](R)-MeQAA was decreased by methyllycaconitine (alpha(7) nAChR antagonist) treatment. In monkeys, alpha(7) nAChRs were highly distributed in the thalamus and cortex but poorly distributed in the cerebellum. The high accumulation was observed in the cortex and thalamus for [(11)C](R)-MeQAA, while the uptake was rather homogeneous for [(11)C](S)-MeQAA.
CONCLUSIONS: [(11)C](R)-MeQAA was successfully synthesized and showed high uptake to the brain. However, since the in vivo selectivity for alpha(7) nAChR was not enough, further PET kinetic analysis or structure optimization is needed for specific visualization of brain alpha(7) nAChRs in vivo. Copyright 2010 Elsevier Inc. All rights reserved.

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Year:  2010        PMID: 20346874     DOI: 10.1016/j.nucmedbio.2009.11.007

Source DB:  PubMed          Journal:  Nucl Med Biol        ISSN: 0969-8051            Impact factor:   2.408


  7 in total

1.  Synthesis and evaluation of new radioligands [(11)C]A-833834 and [(11)C]A-752274 for positron-emission tomography of α7-nicotinic acetylcholine receptors.

Authors:  Andrew G Horti; Hayden T Ravert; Yongjun Gao; Daniel P Holt; William H Bunnelle; Michael R Schrimpf; Tao Li; Jianguo Ji; Heather Valentine; Ursula Scheffel; Hiroto Kuwabara; Dean F Wong; Robert F Dannals
Journal:  Nucl Med Biol       Date:  2013-01-05       Impact factor: 2.408

2.  Human brain imaging of α7 nAChR with [(18)F]ASEM: a new PET radiotracer for neuropsychiatry and determination of drug occupancy.

Authors:  Dean F Wong; Hiroto Kuwabara; Martin Pomper; Daniel P Holt; James R Brasic; Noble George; Boris Frolov; William Willis; Yongjun Gao; Heather Valentine; Ayon Nandi; Lorena Gapasin; Robert F Dannals; Andrew G Horti
Journal:  Mol Imaging Biol       Date:  2014-10       Impact factor: 3.488

3.  Derivatives of dibenzothiophene for positron emission tomography imaging of α7-nicotinic acetylcholine receptors.

Authors:  Yongjun Gao; Kenneth J Kellar; Robert P Yasuda; Thao Tran; Yingxian Xiao; Robert F Dannals; Andrew G Horti
Journal:  J Med Chem       Date:  2013-09-19       Impact factor: 7.446

4.  5-(5-(6-[(11)C]methyl-3,6-diazabicyclo[3.2.0]heptan-3-yl)pyridin-2-yl)-1H-indole as a potential PET radioligand for imaging cerebral α7-nAChR in mice.

Authors:  Yongjun Gao; Hayden T Ravert; Heather Valentine; Ursula Scheffel; Paige Finley; Dean F Wong; Robert F Dannals; Andrew G Horti
Journal:  Bioorg Med Chem       Date:  2012-05-04       Impact factor: 3.641

Review 5.  Nicotinic Acetylcholine Receptors and Microglia as Therapeutic and Imaging Targets in Alzheimer's Disease.

Authors:  Kazuyuki Takata; Hiroyuki Kimura; Daijiro Yanagisawa; Koki Harada; Kaneyasu Nishimura; Yoshihisa Kitamura; Shun Shimohama; Ikuo Tooyama
Journal:  Molecules       Date:  2022-04-27       Impact factor: 4.927

6.  In silico studies of ASEM analogues targeting α7-nAChR and experimental verification.

Authors:  Yang Zhou; Guanglin Kuang; Junhao Li; Christer Halldin; Agneta Nordberg; Bengt Långström; Yaoquan Tu; Hans Ågren
Journal:  RSC Adv       Date:  2021-01-21       Impact factor: 4.036

Review 7.  PET Imaging of the Human Nicotinic Cholinergic Pathway in Atherosclerosis.

Authors:  Matthias Bauwens; Felix M Mottaghy; Jan Bucerius
Journal:  Curr Cardiol Rep       Date:  2015-08       Impact factor: 2.931

  7 in total

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